Epirubicin hydrochloride

Iupac Name：(7S,9S)-7-[(2R,4R,5R)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride

CAS No.: 56390-09-1

Molecular Weight：579.983

Modify Date.: 2023-02-13 23:42

Introduction:

Epirubicin (hydrochloride) is a semisynthetic L-arabino derivative of doxorubicin, and an antineoplastic agent by inhibiting Topoisomerase.

An anthracycline which is the 4'-epi-isomer of doxorubicin. The compound exerts its antitumor effects by interference with the synthesis and function of DNA.

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1. Names and Identifiers

1.1 Name: Epirubicin hydrochloride
1.2 Synonyms: (1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranoside hydrochloride (1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranoside hydrochloride (1:1) (1S,3S)-3-Glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-tetracenyl (5ξ)-3-amino-2,3,6-trideoxy-α-L-erythro-hexopyranoside hydrochloride (1:1) (1S,3S)-3-Glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-tetracenyl 3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranoside hydrochloride (1:1) (8S,10S)-10-{[(2R,4S,5R,6S)-4-Amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracen-5,12-dionhydrochlorid (8S,10S)-10-{[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione hydrochloride 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-.α.-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, hydrochloride 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-, (8S,10S)-, hydrochloride (1:1) 5,12-naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S,10S)-, hydrochloride 5,12-Naphthacenedione, 10-[[(5ξ)-3-amino-2,3,6-trideoxy-α-L-erythro-hexopyranosyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-, (8S,10S)-, hydrochloride (1:1) CS-1396 EINECS 260-145-2 ELLENCE epi-Doxorubicin HCl Epirubicin (hydrochloride) Epirubicin Ebewe EPIRUBICIN HCl Epirubicin HCl (4'-epidoxorubicin) Epirubicin Hydrochloride - CAS 56390-09-1 - Calbiochem PHARMORUBICIN Pidorubicin hydrochloride

1.3 CAS No.: 56390-09-1

1.4 CID: 123134690

1.5 EINECS(EC#): 260-145-2

1.6 Molecular Formula: C27H30ClNO11 (isomer)

1.7 Inchi: InChI=1S/C27H29NO11.ClH/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34;/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3;1H/t10?,13-,15+,17+,22+,27+;/m1./s1

1.8 InChkey: MWWSFMDVAYGXBV-DPZLWMTJSA-N

1.9 Canonical Smiles: CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O.Cl

1.10 Isomers Smiles: CC1[C@@H]([C@@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O.Cl

2. Properties

2.1 Density: 1.61

2.1 Melting point: 185°C dec

2.1 Boiling point: 810.3 °C at 760 mmHg

2.1 Refractive index: 1.709

2.1 Flash Point: 443.8 °C

2.1 Precise Quality: 579.15100

2.1 PSA: 206.07000

2.1 logP: 1.50360

2.1 Solubility: Soluble in DMSO to 100mM, or in ethanol to 10mM

2.2 Λmax: 497(H2O)nm

2.3 Appearance: red to deep red

2.4 Storage: Keep Cold.

2.5 Chemical Properties: Orange-Red Crystalline Solid

2.6 Color/Form: Red, crystalline solid

2.7 Water Solubility: soluble in DMSO to 100mM, or in ethanol to 10mM

2.8 Spectral Properties: Specific optical rotation: +248 deg at 20 deg C/D (0.1% in methanol)
Max absorption (methanol at 56 deg C): 290 nm (epsilon = 145, 1%, 1 cm); 477 nm (epsilon = 225, 1%, 1 cm); 495 nm (epsilon = 223, 1%, 1 cm); 530 nm (epsilon = 124, 1%, 1 cm); 233 nm (epsilon = 658, 1%, 1 cm); 253 nm (epsilon = 440, 1%, 1 cm)

2.9 StorageTemp: Inert atmosphere,Store in freezer, under -20°C

3. Use and Manufacturing

3.1 Usage: Used as an antineoplastic

4. Safety and Handling

4.1 Symbol: GHS07, GHS08

4.1 Hazard Codes: Xn

4.1 Signal Word: Danger

4.1 Risk Statements: 22-63-62-46-40

4.1 Safety Statements: 36/37/38-45-46

4.1 Exposure Standards and Regulations: The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl doxorubicin hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Doxorubicin hydrochloride/

4.2 Octanol/Water Partition Coefficient: log Kow = 1.27

4.3 Other Preventative Measures: PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Principles that apply to chem or biochem lab also apply to microbiological & cell-culture labs ... Special consideration should be given to route of admin. ... Safest method of administering volatile carcinogen is by injection of a soln. Admin by topical application, gavage, or intratracheal instillation should be performed under hood. If chem will be exhaled, animals should be kept under hood during this period. Inhalation exposure requires special equipment. ... Unless specifically required, routes of admin other than in the diet should be used. Mixing of carcinogen in diet should be carried out in sealed mixers under fume hood, from which the exhaust is fitted with an efficient particulate filter. Techniques for cleaning mixer & hood should be devised before expt begun. When mixing diets, special protective clothing &, possibly, respirators may be required. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": When ... admin in diet or applied to skin, animals should be kept in cages with solid bottoms & sides & fitted with a filter top. When volatile carcinogens are given, filter tops should not be used. Cages which have been used to house animals that received carcinogens should be decontaminated. Cage-cleaning facilities should be installed in area in which carcinogens are being used, to avoid moving of ... contaminated /cages/. It is difficult to ensure that cages are decontaminated, & monitoring methods are necessary. Situations may exist in which the use of disposable cages should be recommended, depending on type & amt of carcinogen & efficiency with which it can be removed. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": To eliminate risk that ... contamination in lab could build up during conduct of expt, periodic checks should be carried out on lab atmospheres, surfaces, such as walls, floors & benches, & ... interior of fume hoods & airducts. As well as regular monitoring, check must be carried out after cleaning-up of spillage. Sensitive methods are required when testing lab atmospheres. ... Methods ... should ... where possible, be simple & sensitive. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Rooms in which obvious contamination has occurred, such as spillage, should be decontaminated by lab personnel engaged in expt. Design of expt should ... avoid contamination of permanent equipment. ... Procedures should ensure that maintenance workers are not exposed to carcinogens. ... Particular care should be taken to avoid contamination of drains or ventilation ducts. In cleaning labs, procedures should be used which do not produce aerosols or dispersal of dust, ie, wet mop or vacuum cleaner equipped with high-efficiency particulate filter on exhaust, which are avail commercially, should be used. Sweeping, brushing & use of dry dusters or mops should be prohibited. Grossly contaminated cleaning materials should not be re-used ... If gowns or towels are contaminated, they should not be sent to laundry, but ... decontaminated or burnt, to avoid any hazard to laundry personnel. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Doors leading into areas where carcinogens are used ... should be marked distinctively with appropriate labels. Access ... limited to persons involved in expt. ... A prominently displayed notice should give the name of the Scientific Investigator or other person who can advise in an emergency & who can inform others (such as firemen) on the handling of carcinogenic substances. /Chemical Carcinogens/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Accidental contamination of the health-care environment, resulting in exposure of personnel, patients, visitors, and family members to hazardous substances, is prevented by maintaining the physical integrity and security of packages of hazardous drugs. 1. Access to all areas where hazardous drugs are stored is limited to specified authorized staff. 2. A method should be present for identifying to personnel those drugs that require special precautions (eg, cytotoxics). One way to accomplish this is to apply appropriate warning labels to all hazardous drug containers, shelves, and bins where the drug products are stored. ... 3. A method of identifying, for patients and family members, those drugs that require special precautions in the home should be in place. This may be accomplished in the health-care setting, by providing specific labeling for discharge medications, along with written instructions. 4. Methods for identifying shipping cartons of hazardous drugs should be required from manufacturers and distributors of these drugs. 5. Written procedures for handling damaged packages of hazardous drugs should be maintained. Personnel involved in shipping and receiving hazardous drugs should be trained in these procedures, including the proper use of protective garments and equipment. Damaged shipping cartons of hazardous drugs should be received and opened in an isolated area (eg, in a laboratory fume hood, if available, not in a vertical laminar airflow biological safety cabinet used for preparing sterile products). /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Facilities (eg, shelves, carts, counters, and trays) for storing hazardous drugs are designed to prevent breakage and to limit contamination in the event of leakage. Bins, shelves with barriers at the front, or other design features that reduce the chance of drug containers falling to the floor should be used. Hazardous drugs requiring refrigeration should be stored separately from nonhazardous drugs in individual bins designed to prevent breakage and to contain leakage. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Until the reproductive risks (or lack thereof) associated with handling hazardous drugs within a safety program have been substantiated, staff who are pregnant or breast-feeding should be allowed to avoid contact with these drugs. Policies should be in effect that provide these individuals with alternative tasks or responsibilities if they so desire. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ The pharmacy should provide access to information on toxicity, treatment of acute exposure (if available), chemical inactivators, solubility and stability of hazardous drugs (including investigational agents) used in the workplace. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Appropriate engineering controls should be in place to protect the drug product from microbial contamination and to protect personnel and the environment from the potential hazards of the product. These engineering controls should be maintained according to applicable regulations and standards. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Biological safety cabinets should be cleaned and disinfected regularly to ensure a proper environment for preparation of sterile products. For routine cleanups of surfaces between decontaminations, water should be used (for injection or irrigation) with or without a small amount of cleaner. If the contamination is soluble only in alcohol, then 70% isopropyl or ethyl alcohol may be used in addition to the cleaner. In general, alcohol is not a good cleaner, only a disinfectant, and its use in a biohazard cabinet should be limited. The biohazard cabinet should be disinfected with 70% alcohol before any aseptic manipulation is begun. The excessive use of alcohol should be avoided in biohazard cabinets where air is recirculated ... because alcohol vapors may build up in the cabinet. A lint-free, plastic-backed disposable liner may be used in the biological safety cabinet to facilitate spill cleanup. ... If used, the liner should be changed frequently ... /or/ whenever it is overtly contaminated. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ The biological safety cabinets should be decontaminated on a regular basis (ideally at least weekly) and whenever there is a spill or the biological safety cabinet is moved or serviced, including for certification. ... Currently, no single reagent will deactivate all known hazardous drugs; therefore, decontamination of a biological safety cabinet used for such drugs is limited to removal of contamination from a nondisposable surface (the cabinet) to a disposable surface (eg, gauze or towels) by use of a good cleaning agent that removes chemicals from stainless steel. The cleaning agent selected should have a pH approximating that of soap and be appropriate for stainless steel. Cleaners containing chemicals such as quaternary ammonium compounds should be used with caution, because they may be hazardous to humans and their vapors may build up in any biological safety cabinet where air is recirculated. Similar caution should be used with any pressurized aerosol cleaner; spraying a pressurized aerosol into a biological safety cabinet may disrupt the protective containment airflow, damage the high efficiency particulate air filter, and cause an accumulation of the propellant within a biological safety cabinet where air is recirculated, resulting in a fire and explosion hazard. During decontamination, the operator should wear a disposable closed front gown, disposable latex gloves covered by disposable utility gloves, safety glasses or goggles, a hair covering, and a disposable respirator, because the glass shield of the biological safety cabinet occasionally must be lifted. The blower must be left on, and only heavy toweling or gauze should be used in the biological safety cabinet to prevent it from being "sucked" up the plenum and into the high efficiency particulate air filter. Decontamination should be done from top to bottom (areas of lesser contamination to greater) by applying the cleaner, scrubbing, and rinsing thoroughly with distilled or deionized water. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ The high efficiency particulate air filters /or other exhaust scrubbing system/ of the biohazard cabinet must be replaced whenever they restrict required airflow velocity or if they are overtly contaminated (eg, by a breach in technique that causes hazardous drug to be introduced onto the clean side of the supply high efficiency particulate air filter). Personnel and environmental protection must be maintained during replacement of a contaminated high efficiency particulate air filter. Because replacement of a high efficiency particulate air filter generally requires breaking the integrity of the containment aspect of the cabinet, this procedure may release contamination from the filter into the pharmacy or intravenous preparation area if carried out in an inappropriate manner. Before replacement of a high efficiency particulate air filter contaminated with hazardous drugs, the biological safety cabinet service agent should be consulted for a mutually acceptable procedure for replacing and subsequently disposing of a contaminated high efficiency particulate air filter. One procedure would include moving the biological safety cabinet to a secluded area or using plastic barriers to segregate the contaminated area. Protective clothing and equipment must be used by the servicer. The biological safety cabinet should be decontaminated before filter replacement. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ During removal of gloves, ... avoid touching the inside of the glove or the skin with the contaminated glove fingers. ... The worker should wear a protective disposable gown made of lint free, low-permeability fabric with a solid front, long sleeves, and tight-fitting elastic or knit cuffs when preparing hazardous drugs. Washable garments are immediately penetrated by liquids and therefore provide little, if any protection. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ When double gloving, one glove should be placed under the gown cuff and one over. The glove-gown interface should be such that no skin on the arm or wrist is exposed. Gloves and gowns should not be worn outside the immediate preparation area. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Eyewash fountains should be available in areas where hazardous drugs are routinely handled. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Although noninjectable dosage forms of hazardous drugs contain varying proportions of drug to nondrug (nonhazardous) components, there is potential for personnel exposure and environmental contamination with the hazardous components. Procedures should be developed to avoid the release of aerosolized powder or liquid into the environment during manipulation of these drugs. Drugs designated as hazardous should be labeled or otherwise identified as such to prevent their improper handling. Tablet and capsule forms of these drugs should not be placed in automated counting machines, which subject them to stress and may introduce powdered contaminants into the work area. During routine handling of hazardous drugs and contaminated equipment, workers should wear one pair of gloves of good quality and thickness. The counting and pouring of hazardous drugs should be done carefully, and clean equipment dedicated for use with these drugs should be used. ... When hazardous drug tablets in unit-of-use packaging are being crushed, the package should be placed in a small sealable plastic bag and crushed with a spoon or pestle; caution should be used not to break the plastic bag. Disposal of unused or unusable oral or topical dosage forms of hazardous drugs should be performed in the same manner as for hazardous injectable dosage forms and waste. ... Hazardous drug work areas should have a sink (preferably with an eyewash fountain) and appropriate first aid equipment to treat accidental skin or eye contact according to the protocol. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ A distinctive warning label with an appropriate CAUTION statement should be attached to all hazardous drug materials, consistent with state laws and regulations. This would include, for example, syringes, IV containers, containers of unit-dose tablets and liquids, prescription vials and bottles, waste containers, and patient specimens that contain hazardous drugs. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Supplies of disposable gloves and gowns, safety glasses, disposable plastic-backed absorbent liners, gauze pads, hazardous waste disposal bags, hazardous drug warning labels, and puncture-resistant containers for disposal of needles and ampuls should be conveniently located for all areas where hazardous drugs are handled. Assembling a "hazardous drug preparation and administration kit" is one way to furnish nursing and medical personnel with the materials needed to reduce the risk of preparing and administering a hazardous drug. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Prospective temporary and permanent employees who may be required to work with hazardous drugs should be so notified and should receive adequate information about the policies and procedures pertaining to their use. This notification should be documented during the interview process and retained as part of the employment record for all employees. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ All personnel involved with the transportation, preparation, administration, and disposal of cytotoxic and hazardous substances should continually be updated on new or revised information on safe handling of cytotoxic and hazardous substances. Policies and procedures should be updated accordingly. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ The work area should be designed to provide easy access to those items necessary to prepare, label, and transport final products; contain all related waste; and avoid inadvertent contamination of the work area. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Each health-care setting should have an established first aid protocol for treating cases of direct contact with hazardous drugs, many of which are irritating or caustic and can cause tissue destruction. Medical care providers in each setting should be contacted for input into this protocol. The protocol should include immediate treatment measures and should specify the type and location of medical follow-up and work-injury reporting. Copies of the protocol, highlighting emergency measures, should be posted wherever hazardous drugs are routinely handled. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Only individuals trained to administer hazardous drugs should be allowed to perform this function. Training programs should contain information on the therapeutic and adverse effects of these drugs and the potential, long term health risk to personnel handling these drugs. Each individual's knowledge and technique should be evaluated before administration of these drugs. This should be done by written examination and direct observation of the individual's performance. /Antineoplastic agents/

4.4 Hazard Declaration: H302-H340-H350-H360

4.4 Cleanup Methods: PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Spill kits containing all materials needed to clean up spills of hazardous drugs should be assembled or purchased. These kits should be readily available in all areas where hazardous drugs are routinely handled. If hazardous drugs are being prepared or administered in a nonroutine area (home setting or unusual patient-care area), a spill kit should be obtained by the drug handler. The kit should include two pairs of disposable gloves (one outer pair of utility gloves and one inner latex pair); low-permeability, disposable protective garments (coveralls or gown and shoe covers); safety glasses or splash goggles; respirator; absorbent, plastic-backed sheets or spill pads; disposable toweling; at least 2 sealable thick plastic hazardous waste disposal bags (prelabeled with an appropriate warning label); a disposable scoop for collecting glass fragments; and a puncture-resistant container for glass fragments. All individuals who routinely handle hazardous drugs must be trained in proper spill management and cleanup procedures. Spills and breakages must be cleaned up immediately according to the following procedures. If the spill is not located in a confined space, the spill area should be identified and other people should be prevented from approaching and spreading the contamination. Wearing protective apparel from the spill kit, workers should remove any broken glass fragments and place them in the puncture-resistant container. Liquids should be absorbed with a spill pad; powder should be removed with damp disposable gauze pads or soft toweling. The hazardous material should be completely removed and the area rinsed with water and then cleaned with detergent. The spill cleanup should proceed progressively from areas of lesser to greater contamination. The detergent should be thoroughly rinsed and removed. All contaminated materials should be placed in the disposal bags provided and sealed and transported to a designated containment receptacle. Spills occurring in the biohazard cabinet should be cleaned up immediately; a spill kit should be used if the volume exceeds 150 ml or the contents of one drug vial or ampule. If there is broken glass, utility gloves should be worn to remove it and place it in the puncture-resistant container located in the biohazard cabinet. The biological safety cabinet, including the drain spillage trough, should be thoroughly cleaned. If the spill is not easily and thoroughly contained, the biological safety cabinet should be decontaminated after cleanup. If the spill contaminates the high efficiency particulate air filter, use of the biological safety cabinet should be suspended until the cabinet has been decontaminated and the high efficiency particulate air filter replaced. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ If hazardous drugs are routinely prepared or administered in carpeted areas, special equipment is necessary to remove the spill. Absorbent powder should be substituted for pads or sheets and left in place on the spill for the time recommended by the manufacturer. The powder should then be picked up with a small vacuum unit reserved for hazardous drug cleanup. The carpet should then be cleaned according to usual procedures. The vacuum bag should be removed and discarded or cleaned, and the exterior of the vacuum cleaner should be washed with detergent and rinsed before being covered and stored. The contaminated powder should be discarded into a sealable plastic bag and segregated with other contaminated waste materials. Alternatively, inexpensive wet or dry vacuum units may be purchased for this express use and used with appropriate cleaners. All such units are contaminated, once used, and must be cleaned, stored, and ultimately discarded /properly/ ... The circumstances and handling of spills should be documented. Health-care personnel exposed during spill management should also complete an incident report or exposure form. /Antineoplastic agents/

4.5 DisposalMethods: SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Small quantities of ... some carcinogens can be destroyed using chem reactions ... but no general rules can be given. ... As a general technique ... treatment with sodium dichromate in strong sulfuric acid can be used. The time necessary for destruction ... is seldom known ... but 1-2 days is generally considered sufficient when freshly prepd reagent is used. ... Carcinogens that are easily oxidizable can be destroyed with milder oxidative agents, such as saturated soln of potassium permanganate in acetone, which appears to be a suitable agent for destruction of hydrazines or of compounds containing isolated carbon-carbon double bonds. Concn or 50% aqueous sodium hypochlorite can also be used as an oxidizing agent. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Carcinogens that are alkylating, arylating or acylating agents per se can be destroyed by reaction with appropriate nucleophiles, such as water, hydroxyl ions, ammonia, thiols & thiosulfate. The reactivity of various alkylating agents varies greatly ... & is also influenced by sol of agent in the reaction medium. To facilitate the complete reaction, it is suggested that the agents be dissolved in ethanol or similar solvents. ... No method should be applied ... until it has been thoroughly tested for its effectiveness & safety on material to be inactivated. For example, in case of destruction of alkylating agents, it is possible to detect residual compounds by reaction with 4(4-nitrobenzyl)-pyridine. /Chemical Carcinogens/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ All contaminated disposables should be contained in sealable bags for transfer to larger waste containers. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ All bottles must be discarded as contaminated waste after decontamination of the biohazard cabinet. All protective apparel (gown, gloves, goggles, and respirator) should be discarded as contaminated waste. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ The contaminated filters must be removed, bagged in thick plastic and prepared for disposal in a hazardous waste dump site or incinerator licensed by the Environmental Protection Agency (EPA). /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ The gown should be removed and placed in a sealable container before removal of the inner gloves. The inner gloves should be removed last and placed in the container with the gown. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Hazardous drug waste should be placed in specially marked (specifically labeled CAUTION: HAZARDOUS CHEMICAL WASTE) thick plastic bags or leakproof containers. These receptacles should be kept in all areas where the drugs are commonly used. All and only hazardous drug waste should be placed in them. Receptacles used for glass fragments, needles, and syringes should be puncture resistant. Hazardous drug waste should not be mixed with any other waste. Waste containers should be handled with uncontaminated gloves. ... Gloves, gowns, drug vials, etc, should be sealed in specially labeled (CAUTION: HAZARDOUS CHEMICAL WASTE) thick plastic bags or leakproof containers. ... All hazardous waste collected from drug preparation and patient-care areas should be held in a secure place in labeled, leakproof drums or cartons (as required by state or local regulation or disposal contractor) until disposal. This waste should be disposed of as hazardous or toxic waste in an EPA-permitted state-licensed hazardous waste incinerator. Transport to an offsite incinerator should be done by a contractor licensed to handle and transport hazardous waste. ... If access to an appropriately licensed incinerator is not available, transport to and burial in an EPA-licensed hazardous waste dump site is an acceptable alternative. While there are concerns that destruction of carcinogens by incineration may be incomplete, newer technologies and stringent licensing criteria have improved this disposal method. ... Chemical deactivation of hazardous drugs should be undertaken only by individuals who are thoroughly familiar with the chemicals and the procedures required to complete such a task. The IARC recently published a monograph describing methods for chemical destruction of some cytotoxic (antineoplastic) drugs in the laboratory setting. The chemicals and equipment described, however, are not generally found in the clinical setting, and many of the deactivating chemicals are toxic and hazardous. Most procedures require the use of a chemical fume hood. The procedures are generally difficult, and the deactivation is not always complete. Serious consideration should be given to the negative aspects of chemical deactivation before one commits to such a course of action. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Regulatory agencies such as the EPA and state solid and hazardous waste agencies and local air and water quality control boards must be consulted regarding the classification and appropriate disposal of drugs that are defined as hazardous or toxic chemicals. EPA categorizes several of the antineoplastic agents as toxic wastes, while many states are more stringent and include as carcinogens certain cytotoxic drugs and hormonal preparations. EPA also allows exemptions from toxic waste regulations for small quantity generators, whereas certain states do not. It is critical to research these regulations when disposal procedures are being established. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ If the biological safety cabinets is equipped with a drainpipe and valve, it may be used to collect rinse water. The collection vessel used must fit well around the drain valve and not allow splashing. Gauze may be used around the connection to prevent aerosol from escaping. The collection vessel must have a tight fitting cover, and all rinse water (gauze, if used) must be disposed of as contaminated waste. /Antineoplastic agents/

4.6 RIDADR: NONH for all modes of transport

4.6 Caution Statement: P201-P280-P301 + P312 + P330-P308 + P313

4.6 Formulations/Preparations: ADM
Adriamycin
Adriblastin
Adriblastina
DX

4.7 WGK Germany: 3

4.7 RTECS: QI9295750

4.7 Protective Equipment and Clothing: PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Protective apparel: Disposable closed-front gown or coveralls, disposable utility gloves over disposable latex gloves, NIOSH-approved air-purifying half-mask respirator equipped with a high efficiency filter, and eye protection should be worn. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Class 100 clean-air work stations, both horizontal and vertical airflow (with no containment characteristics), are inappropriate engineering controls for handling hazardous drugs because they provide no personnel protection and permit environmental contamination. Although there are no engineering controls designed specifically for the safe handling of hazardous chemicals as sterile products, Class II contained vertical-flow biological safety cabinets (biohazard cabinets) have been adopted for this use. Biohazard cabinetry is, however, designed for the handling of infectious agents, not hazardous chemicals. ... Based on design, ease of use, and cost considerations, Class II contained-vertical-flow biohazard cabinetry is currently recommended for use in preparing sterile doses of hazardous drugs. Class II cabinetry design and performance specifications are defined in NSF Standard 49. Biological safety cabinets selected for use with hazardous drugs should meet NSF Standard 49 specifications to ensure the maximum protection from these engineering controls. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Workers should wear powder free, disposable surgical latex gloves of good quality when preparing hazardous drugs. Selection criteria for gloves should include thickness (especially at the fingertips where stress is the greatest), fit, length, and tactile sensation. ... The practice of double gloving is supported by research that indicates that many glove materials vary in drug permeability even within lots; therefore, double gloving is recommended. ... In general, surgical latex gloves fit better, have appropriate elasticity for double gloving and maintaining the integrity of the glove-gown interface, and have sufficient tactile sensation (even during double gloving) for stringent aseptic procedures. ... Powdered gloves should be avoided. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Workers who are not protected by the containment environment of a biohazard cabinet should use respiratory protection when handling hazardous drugs. Respiratory protection should be an adjunct to and not a substitute for engineering controls. Surgical masks of all types provide no respiratory protection against powdered or liquid aerosols of hazardous drugs. In situations where workers may be exposed to potential eye contact with hazardous drugs, an appropriate plastic face shield or splash goggles should be worn. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ During compounding of hazardous drugs (eg, crushing, dissolving, and preparing an ointment), workers should wear low permeability gowns and double gloves. Compounding should take place in a protective area such as a disposable glove box. If compounding must be done in the open, an area away from drafts and traffic must be selected, and the worker should use appropriate respiratory protection. /Antineoplastic agents/

4.8 Reactivities and Incompatibilities: Doxorubicin hydrochloride solution is chemically incompatible with heparin sodium injection, and a precipitate may form if the solutions are mixed. Doxorubicin hydrochloride solution also is reportedly incompatible with fluorouracil, and a precipitate may form if the solutions are mixed. The manufacturers recommend that doxorubicin hydrochloride solutions or doxorubicin liposomal dispersion generally not be mixed with other drugs; specialized references should be consulted for specific compatibility information.

4.9 Specification: Orange-Red Crystalline Solid
usageEng:Used as an antineoplastic

4.10 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD50	intravenous	2250ug/kg (2.25mg/kg)	?	Drugs in Japan Vol. -, Pg. 200, 1990.
mouse	LD50	intravenous	31500ug/kg (31.5mg/kg)	?	Drugs in Japan Vol. -, Pg. 200, 1990.
mouse	LD50	oral	> 2gm/kg (2000mg/kg)	?	Drugs in Japan Vol. -, Pg. 200, 1990.
mouse	LD50	subcutaneous	37500ug/kg (37.5mg/kg)	?	Drugs in Japan Vol. -, Pg. 200, 1990.
rat	LD50	intraperitoneal	10800ug/kg (10.8mg/kg)	?	Drugs in Japan Vol. -, Pg. 200, 1990.
rat	LD50	intravenous	17mg/kg (17mg/kg)	?	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 740, 1995.
rat	LD50	oral	1350mg/kg (1350mg/kg)	?	Drugs in Japan Vol. -, Pg. 200, 1990.
rat	LD50	subcutaneous	17600ug/kg (17.6mg/kg)	?	Drugs in Japan Vol. -, Pg. 200, 1990.
women	TDLo	intravenous	1622mg/kg (1622mg/kg)	SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS	Lancet. Vol. 2, Pg. 629, 1986.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

7. Other Information

7.0 Usage: Cell-permeable anthracycline anti-tumor antibiotic

7.1 Description: Epirubicin hydrochloride is an antitumor antibiotic which is epimeric with doxorubicin a t the 4’-position of the amino sugar moiety. It has shown utility in the treatment of mammary, gastric, colorectal, pulmonary and ovarian carcinomas, as well as malignant lymphoma and melanoma and soft tissue sarcoma. It is reported to be less sardiotoxic than doxorubicin.

7.2 Description: Epirubicin is a stereoisomer of the antitumor anthracycline doxorubicin (Item No. 15007) that undergoes β-glucuronidation, which partially detoxifies the dose-limiting side effects that are present with doxorubicin. Compared to doxorubicin, epirubicin is equally cytotoxic to HeLa cells (ID₅₀s = 9 μM). When used either alone or in combination therapies, epirubicin has been shown to demonstrate high rates of complete or partial remission in various cancers including advanced ovary, lymphomas, breast, pancreas, gastric, hepatocellular carcinoma, head and neck tumors, and colorectal.

7.3 Chemical Properties: Orange-Red Crystalline Solid

7.4 Originator: Erbamont (Italy)

7.5 Uses: Used as an antineoplastic

7.6 Brand name: Ellence(Pfizer);FARMORUBICIN.

7.7 Biological Functions: This stereoisomer of doxorubicin has the 4′-hydroxy group of the daunosamine sugar oriented in the β-position . Epirubicin will be slowly reduced to the active C13 alcohol (epirubicinol), giving it a 30- to 38-hour half life, which is similar to that of doxorubicin. Unlike doxorubicinol, however, which was equally active with doxorubicin, epirubicinol has only one-tenth the activity of its parent drug and is not believed to contribute significantly to the therapeutic action of this agent.

7.8 Biological Activity: Antibiotic antitumor agent. Inhibits the synthesis and function of DNA (IC 50 = 62.7 μ M in rat glioblastoma cell lines) and inhibits the relaxing property of topoisomerase II.

7.9 Clinical Use: Epirubicin is indicated for use in breast cancer, and the starting dose is 100 to 120 mg/m2 (compared to a starting dose of 60–75 mg/m2 for doxorubicin).

7.10 Side effects: The side effects and precautions are as outlined previously for doxorubicin, although there is a lower risk of serious myocardial toxicity or myelotoxicity.

7.11 Metabolism: Cleavage of the epimerized sugar will occur before excretion, generating an aglycone that is indistinguishable from that generated by doxorubicin. Although excretion is primarily biliary, dosage reduction in severe renal impairment, as well as in hepatic dysfunction, is warranted.

7.12 Mesh: Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II. (See all compounds classified as Topoisomerase II Inhibitors.)|Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

7.13 Mesh Entry Terms: Adriablastin|4' Epi Adriamycin

8. Computational chemical data

Molecular Weight: 579.983g/mol
Molecular Formula: C₂₇H₃₀ClNO₁₁
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 579.1507385
Monoisotopic Mass: 579.1507385
Complexity: 977
Rotatable Bond Count: 5
Hydrogen Bond Donor Count: 7
Hydrogen Bond Acceptor Count: 12
Topological Polar Surface Area: 206
Heavy Atom Count: 40
Defined Atom Stereocenter Count: 5
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 2
CACTVS Substructure Key Fingerprint: AAADceB6PAAEAAAAAAAAAAAAAAAAAAAAAAA0YMGCAAAAAADBQAAAHgAQCAAADHzxmAcyDoBABgCIAqBSAAICCAAkIAAIiIFGCMgfNzaGtRqicWAn8BEPuYfL7PzOwQADAAAYAADCAAYQADAAAAAAAAAAAA==

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